JPS6178801A - Production of substituted silylpropyl group-containing cellulose derivative - Google Patents

Production of substituted silylpropyl group-containing cellulose derivative

Info

Publication number
JPS6178801A
JPS6178801A JP20010084A JP20010084A JPS6178801A JP S6178801 A JPS6178801 A JP S6178801A JP 20010084 A JP20010084 A JP 20010084A JP 20010084 A JP20010084 A JP 20010084A JP S6178801 A JPS6178801 A JP S6178801A
Authority
JP
Japan
Prior art keywords
group
cellulose derivative
substituted
derivative
organosilicon compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
JP20010084A
Other languages
Japanese (ja)
Other versions
JPS6411201B2 (en
Inventor
Minoru Takamizawa
高見沢 稔
Toru Chiba
徹 千葉
Akira Yamamoto
昭 山本
Kazumasa Maruyama
丸山 和政
Shigehiro Nagura
茂広 名倉
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shin Etsu Chemical Co Ltd
Original Assignee
Shin Etsu Chemical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shin Etsu Chemical Co Ltd filed Critical Shin Etsu Chemical Co Ltd
Priority to JP20010084A priority Critical patent/JPS6178801A/en
Publication of JPS6178801A publication Critical patent/JPS6178801A/en
Publication of JPS6411201B2 publication Critical patent/JPS6411201B2/ja
Granted legal-status Critical Current

Links

Abstract

PURPOSE:To obtain a cellulose derivative having a film-forming property, toughness, gas permeability and excellent electrical properties, by effecting an addition reaction between an alkylcellulose derivative and a specified organosilicon compound. CONSTITUTION:A substituted silylpropyl group-containing cellulose derivative of formula II is obtained by effecting an addition reaction between an alkylcellulose derivative of formula I and an organosilicon compound having at least one identical SiH bond in the molecule. In formula I, Cell is a residue of cellulose or its derivative. In formula II, R<1>, R<2> and R<3> are each a 1-8C monovalent hydrocarbon, 1-8C monovalent halohydrocarbon, 1-4C alkoxy or organosiloxy group, including the case where two of R<1>-R<3> may be combined to form a cyclic organosiloxy group. In the above reaction, the purpose compound can be obtained quantitatively by adding chloroplatinic acid, rhodium catalyst or the like to the reaction system as a catalyst for promoting the reaction and adding an organosilicon compound thereto while heating the mixture to 40 deg.C or higher.

Description

【発明の詳細な説明】 (産業上の利用分野) 本発明はアリルセルロース誘導体に有機けい素化合物を
反応させることにより置換シリルプロピル基含有セルロ
ース誘導体を製造する方法C:関する。
DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to method C for producing a substituted silylpropyl group-containing cellulose derivative by reacting an allylcellulose derivative with an organosilicon compound.

(発明の目的) 従来のセルロース誘導体がもつ造膜性1強じん性等の特
性と有機けい素化合物がもつガス透過性、電気特性等の
特性を併せ具備した、ガス分離膜。
(Object of the invention) A gas separation membrane that combines the properties of conventional cellulose derivatives, such as film-forming properties and toughness, with the properties of organosilicon compounds, such as gas permeability and electrical properties.

接着剤、塗料、繊維処理剤などとして有用とされるセル
ロース誘導体の提供を目的とする。
The objective is to provide cellulose derivatives that are useful as adhesives, paints, fiber treatment agents, etc.

(発明の構成) 本発明者らはアリルセルロース誘導体とR81−H結合
を有する有機けい素化合物が定量的に付加反応し、有機
けい素化合物が化学的に導入されたセルロース誘導体が
容易に得られることを見出し本発明を完成した。
(Structure of the Invention) The present inventors have demonstrated that an allyl cellulose derivative and an organosilicon compound having an R81-H bond undergo a quantitative addition reaction, and a cellulose derivative into which an organosilicon compound is chemically introduced can be easily obtained. They discovered this and completed the present invention.

すなわち、本発明は一般式 %式%(1) (式中のCellはセルロースおよびセルロース誘導体
の残基な示す)で表わされるアリルセルロース誘導体(
二、1分子中に少なくとも1個のミ5i−H結合を有す
る有機けい素化合物を付加反応させることを特徴とする
、一般式 %式%(1) (式中のR1、R2、R3は1個々C:、炭素原子数1
〜8の一価炭化水素基もしくはハクゲン化−価炭化水素
基、炭素原子数1〜4のアルコキン基、オルガノシロキ
レ基から選択される基、またはR1へR3のうち2つが
共になって環状のオルガノシロキシ基を形成する場合を
含む、Ce1Lは前記と同じ)で表わされる置換シリル
プロピル基含有セルロース誘導体の製造方法に関するも
のである。
That is, the present invention provides an allyl cellulose derivative (
2. General formula % formula % (1) (in the formula, R1, R2, R3 are 1 Individual C:, number of carbon atoms 1
A group selected from a monovalent hydrocarbon group or a halogenated-valent hydrocarbon group of ~8, an alkoxy group having 1 to 4 carbon atoms, an organosilokyle group, or two of R1 and R3 together form a cyclic The present invention relates to a method for producing a substituted silylpropyl group-containing cellulose derivative represented by (Ce1L is the same as above), including the case where an organosiloxy group is formed.

以下本発明の詳細な説明する。The present invention will be explained in detail below.

本発明に使用される前記一般式(I)で示されるアリル
セルロースエーテルは、セルロースモジくはセルロース
誘導体におけるグルコース単位中の水酸基が式−ocp
、aH−ca、(アリロキシ基)で示される基で置換し
たものであり、これにはアリルセルロース、アリルメチ
ルセルロース、アリルエチルセルロース、アリルメチル
ヒドロキシプロピルセルロース、アリルアセチルセルロ
ースが例示される。これらのアリルセルロース1M導体
は。
The allylcellulose ether represented by the general formula (I) used in the present invention has a hydroxyl group in the glucose unit in the cellulose module or cellulose derivative having the formula -ocp
, aH-ca, (allyloxy group), and examples thereof include allyl cellulose, allyl methyl cellulose, allyl ethyl cellulose, allyl methylhydroxypropyl cellulose, and allyl acetyl cellulose. These allylcellulose 1M conductors.

そのアリロキシ基の置換度(O,S、)が0.1以上で
あることが望ましく、0.1よりも少ない置換度のもめ
であると、後記する有機けい素化合物の反応する割合が
相対的(;小さくなり、有機けい素化合物の特性導入が
不充分となる。
It is desirable that the degree of substitution (O, S,) of the allyloxy group is 0.1 or more, and if the degree of substitution is less than 0.1, the reaction rate of the organosilicon compound described later will be relatively low. (; becomes small, and the characteristics of the organosilicon compound are insufficiently introduced.

一方上記アリルセルロース誘導体と反応させる分子中ζ
ニミ5i−H結合を有する有機けい素化合物は、一般式 %式% で示されるもので1式中のR1,R2,RF  は個々
に、炭素原子数1〜8の一価炭化水素基もしくはハロゲ
ン化−価炭化水素基、炭素原子数1〜4のアルコキシ基
から選択される基であるオルガノシラン化合物、ならび
I:それらのR1へR3のうち少なくとも1個がオルガ
ノシロキシ基であるか、またはR1へR3のうち2つが
共E:なって環状のオルガノシロキシ基を形成している
オルガノポリシロキサン化合物から広く選択される。
On the other hand, ζ in the molecule to be reacted with the above allylcellulose derivative
An organosilicon compound having a NiMI5i-H bond is represented by the general formula %, where R1, R2, and RF each represent a monovalent hydrocarbon group having 1 to 8 carbon atoms or a halogen. an organosilane compound which is a group selected from a valent hydrocarbon group, an alkoxy group having 1 to 4 carbon atoms, and I: at least one of those R1 to R3 is an organosiloxy group, or R1 It is widely selected from organopolysiloxane compounds in which two of R3 are co-E to form a cyclic organosiloxy group.

上記オルガノンラン化合物としては具体的に次のちのが
例示される。ただし以下の記載において、Meはメチル
基、Etはエチル基、Prはプロピル基、phはフェニ
ル基をそれぞれ示す。
Specific examples of the above organonrane compounds include the following. However, in the following description, Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, and ph represents a phenyl group.

H−81(Me>   、H−at (gt)sp−s
t (Pr)   、  )T−51(ph>3.H−
Si (Me)2(Ph)、H−st (mt)、(p
h)、E −S i (Me> 、 (OH,OH・、
CiF、入H−8i (Me +(Ph)2、H−Si
 (Ph32(CiH,Of(、OF、)。
H-81 (Me> , H-at (gt) sp-s
t (Pr), )T-51 (ph>3.H-
Si (Me)2 (Ph), H-st (mt), (p
h), E −S i (Me>, (OH, OH・,
CiF, H-8i (Me + (Ph)2, H-Si
(Ph32(CiH,Of(,OF,).

)T−Si (OMe)   、  H−Si (OE
t)3 、H−Si (MeHOMs)   H−8i
(MsHOEt>2゜H−81(EtHOHt)z 、
H−S i (Fi t3 (OMe)2 。
) T-Si (OMe), H-Si (OE
t)3, H-Si (MeHOMs) H-8i
(MsHOEt>2゜H-81(EtHOHt)z,
H-S i (Fi t3 (OMe)2.

H−81(pbHOMe)、、 H−si(phi(o
gz>、、またオルガノポリシロキサン化合物としては
、線状給進1仔枝構造、環状構造のいずれも包含し、こ
れらの各オルガノポリシロキサン化合物における有機基
(けい素原子C:結合する有機基)は、炭素原子数1〜
8の一価炭化水素基もしくはハロゲン化−偏成化水素基
、炭素原子数1〜4のアルコキシ基から選択される。具
体的例示をあげれば次のとおりである。
H-81(pbHOMe), H-si(phi(o
gz>,,The organopolysiloxane compound includes both a linear fed single branch structure and a cyclic structure, and the organic group (silicon atom C: bonding organic group) in each of these organopolysiloxane compounds. has 1 to 1 carbon atom
8 monovalent hydrocarbon groups, halogenated-polarized hydrogen groups, and alkoxy groups having 1 to 4 carbon atoms. Specific examples are as follows.

Me    Me            Me   
 Mel      1              
1     1H−8i−0−8i−Me、   H−
8i−0−8i−OEt  。
Me Me Me
Mel 1
1 1H-8i-0-8i-Me, H-
8i-0-8i-OEt.

Me    Me            Me   
 MeMe    Ph           Me 
   Mel      1            
1     1H−8i−0−8i−Ph  %、H−
8i−0−8i−Me  。
Me Me Me
MeMe Ph Me
Mel 1
1 1H-8i-0-8i-Ph%, H-
8i-0-8i-Me.

Me    Ph           Ph    
MeMe     Me M 6     M e I Me    Me           Me    
PhH−8i−0−8i−HlH−3i−0−8i−H
Me Ph Ph
Me Me Me M 6 Me Me Me Me Me Me
PhH-8i-0-8i-HlH-3i-0-8i-H
.

I      I             1   
  1Ms    Me           Me 
   Ph(n≧1 ) (n≧1 ) (m≧l、n≧0) (vl:ビニル基、m≧1.n≧0H Rニー0H2CH20F3 % m≧1.n≧0Ht≧
1.m≧1.n≧0) MeO−8iMe3 H−8i−0−8i−0−8iMe3 MeO−8iMa。
I I 1
1Ms Me Me
Ph(n≧1) (n≧1) (m≧l, n≧0) (vl: vinyl group, m≧1.n≧0H Rnee0H2CH20F3 % m≧1.n≧0Ht≧
1. m≧1. n≧0) MeO-8iMe3 H-8i-0-8i-0-8iMe3 MeO-8iMa.

(Q : −0−8i Me3、m≧1.n≧1)m=
1.2.3または4 n=o 、 1 、2または3 m+n=3.4または5 m=1.2.3または4 n=o 、 1 、2または3 0+n=3.4または5 以上例示したESi−1(結合を有する有機けい素化合
物は、1種類のみに限られずそれらの2種以上を組合わ
せて使用してもよい。
(Q: -0-8i Me3, m≧1.n≧1) m=
1.2.3 or 4 n=o, 1, 2 or 3 m+n=3.4 or 5 m=1.2.3 or 4 n=o, 1, 2 or 3 0+n=3.4 or 5 More examples The ESi-1 (organosilicon compound having a bond) is not limited to one type, and two or more types thereof may be used in combination.

本発明の方法は前記アリルセルロース誘導体l:、ミ5
i−H結合を有する有機けい素化合物を付加反応させる
ことにより目的とする置換シリルプロビル基含有セルロ
ース誘導体を得るのであるが、この反応を具体的シニ説
明すれば次のとおりである。
The method of the present invention is based on the allyl cellulose derivative l:, mi5.
The desired substituted silylprobyl group-containing cellulose derivative is obtained by carrying out an addition reaction with an organosilicon compound having an i-H bond, and a detailed explanation of this reaction is as follows.

まず、アリルセルロース誘導体を、ベンゼン、トルエン
、キシレンなどの芳香族炭化水素、クロロホルム、ジク
ロルエタンなどのハロゲン化炭化水素、あるいはテトラ
ヒドロフランなどの溶剤C二溶解もしくは分散させ、こ
の系にミ5i−H結合を有する有機けい素化合物を添加
し、60℃以上好ましくは80〜150’C1二加熱す
ること1;より、有機けい素化合物I:おけるESi−
Hとセルロース誘導体C:おけるアリル基との間で付加
反応が進行し目的の置換シリルプロピル基含有セルロー
ス誘導体が得られる。
First, an allylcellulose derivative is dissolved or dispersed in an aromatic hydrocarbon such as benzene, toluene, or xylene, a halogenated hydrocarbon such as chloroform or dichloroethane, or a solvent C2 such as tetrahydrofuran, and a mi5i-H bond is added to this system. The organic silicon compound I: ESi-
An addition reaction proceeds between H and the allyl group in the cellulose derivative C: to obtain the desired substituted silylpropyl group-containing cellulose derivative.

上記反応に当って反応を促進させるための触媒として塩
化白金酸、塩化白金酸とオレフィンとのコンプレックス
、塩化白金酸とビニル甚含有有機けい素化合物との反応
物、あるいはロジウム系触媒を反応系に存在させ、40
℃以上に加熱しながら有機けい素化合物を添加して反応
させることにより、定量的1:置換シリルプロピル基含
有セルロース′誘導体を得ることができる。
As a catalyst for promoting the above reaction, chloroplatinic acid, a complex of chloroplatinic acid and an olefin, a reaction product of chloroplatinic acid and a vinyl-containing organosilicon compound, or a rhodium-based catalyst is used in the reaction system. exist, 40
By adding and reacting an organosilicon compound while heating to a temperature above .degree. C., a quantitative 1:substituted silylpropyl group-containing cellulose' derivative can be obtained.

なお、アリルセルロース誘導体とミ5i−H結合金有有
機けい素化合物とは定量的に反応するので、通常の場合
はセルロース誘導体のアリル基の全モル数と有機けい素
化合物シーおけるESi−H結合の全モル数が当モルと
なる仕込みで反応させることが望ましい。もちろんいず
れかを不足のモル数で仕込むことC:より、アリル基も
しくはミ5i−H結合を生成物の分子中(二残存させる
ことができるう さらl二別の反応のさせ方としては、アリルセルロース
誘導体と =8i−H結合を有する有機けい素化合物を
所定の割合でトルエン、キシレン、テトラヒドロフラン
などの溶剤中に溶解させたのち塩化白金酸などの触媒を
加えて板状、フィルム状、糸状、中空繊維状等(:成形
し、この成形時あるいは成形後に加熱処理することによ
り両者の付加反応を行わせる方法C二より成形された目
的物を得ることができる。
In addition, since the allylcellulose derivative and the organosilicon compound having a 5i-H bond react quantitatively, in the normal case, the total number of moles of allyl groups in the cellulose derivative and the ESi-H bond in the organosilicon compound react with each other quantitatively. It is desirable to carry out the reaction in such a manner that the total number of moles of is equivalent to the molar amount. Of course, it is necessary to prepare an insufficient number of moles of either of them. A cellulose derivative and an organosilicon compound having an =8i-H bond are dissolved in a solvent such as toluene, xylene, or tetrahydrofuran at a predetermined ratio, and then a catalyst such as chloroplatinic acid is added to form a plate, film, thread, etc. A molded object can be obtained by method C2, in which hollow fibers, etc. are molded and heat-treated during or after molding to cause an addition reaction between the two.

本発明の方法(二より得られる置換シリルプロピル基含
有セルロース誘導体は、セルロース誘導体がもつ造膜性
、強じん性等の特性と有機けい素化合物がもつガス透過
性、電気特性等の特性を併せ具備しているので、ガス分
離膜、接着剤、塗料、繊維処理剤などとして有用とされ
るものである。
The substituted silylpropyl group-containing cellulose derivative obtained by the method (2) of the present invention combines the properties of cellulose derivatives, such as film-forming properties and toughness, with the properties of organosilicon compounds, such as gas permeability and electrical properties. Therefore, it is useful as gas separation membranes, adhesives, paints, fiber treatment agents, etc.

つぎf二具体的実施例をあげる。Next, f2 concrete examples will be given.

実施例1〜4 アリルセルロース(アリル基のり、S、=2.0)5ノ
をテトラヒドロフラン100m1二溶解し、2%塩化白
金酸−n−ブタノール溶液なQ、Qlm加えたのち66
°CC二昇温し、$1表(;示した有機けい素化合物を
0.042モルを滴下し反応させた。
Examples 1 to 4 Five parts of allyl cellulose (allyl group glue, S, = 2.0) were dissolved in 100 ml of tetrahydrofuran, and 2% chloroplatinic acid-n-butanol solution Q and Qlm were added thereto.
The temperature was raised to 2°C, and 0.042 mol of the organosilicon compound shown in the table was added dropwise to react.

反応液を大量の水−メタノール(1:l容量比)中へか
くはんしながら注ぎ生じた析出物をf別し繰返し水洗し
たのち乾燥した。収量はそれぞれ第1表I:示すとおり
であった。
The reaction solution was poured into a large amount of water-methanol (1:l volume ratio) with stirring, and the resulting precipitate was separated, washed repeatedly with water, and then dried. The yields were as shown in Table 1.

つぎ(;各生成物をトルエンC;溶解しキャスティング
法C二より厚さ10trrnのフィルムなつくり、赤外
線吸収スペクトル分析C;より調べたところ、いずれ【
二ついても、アリル基に特徴的な309〇cm−1,1
645an   、  995cm−,1,910cm
−”  の吸収は全くなくなっており、かわ各月;メチ
レン基の吸収1450crn−’とメチルシロキチンの
吸収1260an−1,840cm−’  、7803
 ’が新たに大きくでていた。これらのことからアリル
セルロースのアリル基に有機けい素化合物の=Si−H
が定量的に付加し置換シリルプロピルセルロースが生成
されたことが確認された。
Next, each product was dissolved in toluene C, and a film with a thickness of 10 trrn was made using casting method C2. Infrared absorption spectrum analysis C;
Both are 3090cm-1,1, which is characteristic of allyl groups.
645an, 995cm-, 1,910cm
-" absorption has completely disappeared, and the absorption of methylene group is 1450 crn-' and the absorption of methylsilochitin is 1260 an-1,840 cm-', 7803
' was newly larger. Based on these facts, the allyl group of allyl cellulose has an organosilicon compound =Si-H.
It was confirmed that silylpropylcellulose was quantitatively added and substituted silylpropylcellulose was produced.

一方上記各フイルムについて引張り強さと気体透過係数
を測定したつ結果を第1表f二示す。
On the other hand, the results of measuring the tensile strength and gas permeability coefficient of each of the above films are shown in Table 1.

第1表C二示す結果から明らかなとおり、置換シリルプ
ロピルセルロースはセルロースのもつ膜の強さとけい素
化合物のもつり体透過性の両性質を兼備しており、特I
ニガス分離腹としての用途に有用とされるものである。
As is clear from the results shown in Table 1, C2, substituted silylpropyl cellulose has both the membrane strength of cellulose and the stent body permeability of silicon compounds, and has special characteristics.
It is said to be useful as a gas separation belly.

実施例5〜7 解させ、2%の塩化白金酸−ブタノール溶液を0.01
−加えたのち、第2表に示した有機けい素化合物を同表
に示す量、反応温度66℃(二で、滴下反応させた。反
応終了後テトラヒドロフランを減圧下で留去したところ
、それぞれ第2表に示した収量で反応生成物が得られた
Examples 5-7 A 2% chloroplatinic acid-butanol solution was added to 0.01
- After addition, the organosilicon compounds shown in Table 2 were added in the amounts shown in the same table, and the reaction temperature was 66°C. The reaction product was obtained in the yield shown in Table 2.

各反応生成物(二ついて前例と同様にして赤外線吸収ス
ペクトル分析C二より調べた結果、置換シリルプロピル
アセチルセルロースであることが1ii認された。
As a result of examining each reaction product (two of them) using infrared absorption spectroscopy C2 in the same manner as in the previous example, it was confirmed that they were substituted silylpropyl acetyl cellulose.

このよう(ニして得られた置換シリルプロピルアセチル
セルロースは、シリル基(ニアルコキシル基が置換して
いるため、突気中の水分などで容易に加水分解し三次元
ポリマーになり、強固な接着剤や塗料などの一用途f;
有用とされる。
Substituted silylpropyl acetyl cellulose obtained in this manner is substituted with a silyl group (nialkoxyl group), so it is easily hydrolyzed by moisture in the air, etc., and becomes a three-dimensional polymer, resulting in strong adhesive properties. One use for agents, paints, etc. f;
Considered useful.

実施例8 アリルエチルセルロース(アリル基のり、 8. =0
.2、エチル基のり、S、=2.5)  5Pをトルエ
ン100sdC溶解し、これに次式 のオルガノポリシロキサン3?を添加し溶解したのち、
塩化白金酸とテトラビニルテトラメチルテトランクロへ
キチンとの反応物をpt量として、2X10−’tとな
るようイ;加えて均一に混合した。この溶液からキャス
ティングC二より厚さ10μmのフィルムをつくり、1
30℃1:2時間加熱したのち、赤外線吸収スペクトル
分析で調べた結果、置換シリルプロピル基含有セルロー
ス誘導体となっていることが確認された。
Example 8 Allyl ethyl cellulose (allyl group glue, 8. =0
.. 2. Ethyl group glue, S, = 2.5) Dissolve 5P in toluene at 100 sdC, and add organopolysiloxane 3? of the following formula to this. After adding and dissolving,
A reaction product of chloroplatinic acid and tetravinyltetramethyltetranchlorohechitin was added so as to have a pt amount of 2×10-'t, and was mixed uniformly. A film with a thickness of 10 μm was made from this solution using Casting C2, and
After heating at 30° C. for 1:2 hours, an infrared absorption spectrum analysis confirmed that the product was a substituted silylpropyl group-containing cellulose derivative.

またこのフィルムの引張り強さは435Kp/catで
あり、酸素透過係数がPO4−7,4X  10−’a
d(STP) an /at−sea−an Hg  
とすぐれており気体分離膜として有用とされる。
In addition, the tensile strength of this film is 435 Kp/cat, and the oxygen permeability coefficient is PO4-7,4X 10-'a
d(STP) an /at-sea-an Hg
It is considered to be useful as a gas separation membrane.

Claims (1)

【特許請求の範囲】 1、一般式Cell−OCH_2CH=CH_2(式中
のCellはセルロースおよびセルロース誘導体の残基
を示す)で表わされるアリルセルロース誘導体に、1分
子中に少なくとも1個の≡Si−H結合を有する有機け
い素化合物を付加反応させることを特徴とする、一般式
▲数式、化学式、表等があります▼(式中のR^1、R
^2、R^3は、個々に、炭素原子数1〜8の一価炭化
水素基もしくはハロゲン化一価炭化水素基、炭素原子数
1〜4のアルコキシ基、オルガノシロキシ基から選択さ
れる基、またはR^1〜R^3のうち2つが共になって
環状のオルガノシロキシ基を形成する場合を含む、Ce
llは前記と同じ)で表わされる置換シリルプロピル基
含有セルロース誘導体の製造方法 2、前記アリルセルロース誘導体として、アリル基置換
度(D.S.)0.1以上のものを使用する特許請求の
範囲第1項記載の置換シリルプロピル基含有セルロース
誘導体の製造方法 3、前記有機けい素化合物として、分子中に≡Si−H
結合を有するオルガノシラン化合物を使用する特許請求
の範囲第1項記載の置換シリルプロピル基含有セルロー
ス誘導体の製造方法 4、前記有機けい素化合物として、分子中に≡Si−H
結合を有するオルガノポリシロキサン化合物を使用する
特許請求の範囲第1項記載の置換シリルプロピル基含有
セルロース誘導体の製造方法
[Claims] 1. At least one ≡Si- There are general formulas ▲mathematical formulas, chemical formulas, tables, etc.▼(R^1, R
^2 and R^3 are each a group selected from a monovalent hydrocarbon group having 1 to 8 carbon atoms, a halogenated monovalent hydrocarbon group, an alkoxy group having 1 to 4 carbon atoms, and an organosiloxy group. , or two of R^1 to R^3 together form a cyclic organosiloxy group, Ce
Method 2 for producing a substituted silylpropyl group-containing cellulose derivative represented by (ll is the same as above), Claims in which an allyl cellulose derivative having an allyl group substitution degree (D.S.) of 0.1 or more is used. 3. Method 3 for producing a substituted silylpropyl group-containing cellulose derivative according to item 1, wherein the organosilicon compound is ≡Si-H in the molecule.
A method 4 for producing a substituted silylpropyl group-containing cellulose derivative according to claim 1, which uses an organosilane compound having a bond, wherein the organosilicon compound contains ≡Si-H in the molecule.
A method for producing a substituted silylpropyl group-containing cellulose derivative according to claim 1, which uses an organopolysiloxane compound having a bond.
JP20010084A 1984-09-25 1984-09-25 Production of substituted silylpropyl group-containing cellulose derivative Granted JPS6178801A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP20010084A JPS6178801A (en) 1984-09-25 1984-09-25 Production of substituted silylpropyl group-containing cellulose derivative

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP20010084A JPS6178801A (en) 1984-09-25 1984-09-25 Production of substituted silylpropyl group-containing cellulose derivative

Publications (2)

Publication Number Publication Date
JPS6178801A true JPS6178801A (en) 1986-04-22
JPS6411201B2 JPS6411201B2 (en) 1989-02-23

Family

ID=16418842

Family Applications (1)

Application Number Title Priority Date Filing Date
JP20010084A Granted JPS6178801A (en) 1984-09-25 1984-09-25 Production of substituted silylpropyl group-containing cellulose derivative

Country Status (1)

Country Link
JP (1) JPS6178801A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02115190A (en) * 1988-10-21 1990-04-27 Shin Etsu Chem Co Ltd Fluorine-containing organosilicon compound
JPH02283701A (en) * 1989-03-03 1990-11-21 Natl Starch & Chem Corp Polysaccharide containing organosiloxane
JP2001002702A (en) * 1999-06-18 2001-01-09 Toppan Printing Co Ltd Cellulose and its production
JP2001278901A (en) * 2000-02-15 2001-10-10 Clariant Gmbh Modified cellulose ether provided with hydrophobicity, and production method and use thereof
WO2014084069A1 (en) * 2012-11-29 2014-06-05 学校法人芝浦工業大学 Adhesive and laminate, and processes for producing both
JP2014215592A (en) * 2013-04-30 2014-11-17 コニカミノルタ株式会社 Glass with polarization function and liquid crystal display device provided therewith
JP2014240447A (en) * 2013-06-11 2014-12-25 信越化学工業株式会社 Adhesive derived from lignocellulose and wooden composite material using the same

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02115190A (en) * 1988-10-21 1990-04-27 Shin Etsu Chem Co Ltd Fluorine-containing organosilicon compound
JPH02283701A (en) * 1989-03-03 1990-11-21 Natl Starch & Chem Corp Polysaccharide containing organosiloxane
JP2001002702A (en) * 1999-06-18 2001-01-09 Toppan Printing Co Ltd Cellulose and its production
JP2001278901A (en) * 2000-02-15 2001-10-10 Clariant Gmbh Modified cellulose ether provided with hydrophobicity, and production method and use thereof
WO2014084069A1 (en) * 2012-11-29 2014-06-05 学校法人芝浦工業大学 Adhesive and laminate, and processes for producing both
JPWO2014084069A1 (en) * 2012-11-29 2017-01-05 学校法人 芝浦工業大学 Adhesive and laminate, and production method thereof
JP2014215592A (en) * 2013-04-30 2014-11-17 コニカミノルタ株式会社 Glass with polarization function and liquid crystal display device provided therewith
JP2014240447A (en) * 2013-06-11 2014-12-25 信越化学工業株式会社 Adhesive derived from lignocellulose and wooden composite material using the same

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